Formic Acid → Statine

HRID 1045312Notes

Reaction equation

HRID 1045312 reaction equation
CC[C@@H]([C@H](N[C:34]([CH2:36][C@H:37]([OH:70])[C@@H:38]([NH:43]C([C@@H](N(C([C@@H](NC([C@H](O)[C@H](CC)C)=O)CC(C)C)=O)C)CCC(N)=O)=O)[CH2:39][CH:40]([CH3:42])[CH3:41])=[O:35])C(NCC(N([C@@H](C(N1[C@H](C(OC)=O)CCC1)=O)CC1C=CC=CC=1)C)=O)=O)C.CC(C[C@H](NC1C([N+]([O-])=O)=CC([N+]([O-])=O)=C(F)C=1)C(N)=[O:77])C.CO.C(O)=O>O>[NH2:43][C@H:38]([C@H:37]([CH2:36][C:34](=[O:35])[OH:77])[OH:70])[CH2:39][CH:40]([CH3:42])[CH3:41]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 887Methanol2×HCID 15817226N~2~-(5-Fluoro-2,4-dinitrophenyl)-L-leucinamideHCID 44253975Grassystatin C

Product 1

HCID 123915Statine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Samples of both compounds 1 and 3 (35 μg) were subjected to acid hydrolysis, derivatized with L-FDLA, and analyzed by reversed-phase HPLC [column, Alltima HP C18 HL (4.6×250 mm), 5 μm, Alltech; flow rate, 0.5 mL/min; detection by ESIMS in negative ion mode (MRM scan, 468→408)], using a linear gradient of MeOH in H2O (both containing 0.1% HCOOH, 40-100% MeOH over 50 min). Two peaks, corresponding to (3S,4S)-Sta-L-FDLA and (3R,4S)-Sta-L-FDLA, were observed in both samples in a 1:1 ratio at tR 35.5 and 35.9 min, respectively. The retention times (tR, min) of the authentic standards were as follows: (3S,4S)-Sta-L-FDLA (35.5), (3R,4S)-Sta-L-FDLA (35.9), (3S,4S)-Sta-D-FDLA [corresponding to (3R,4R)-Sta-L-FDLA, 45.7], (3R,4S)-Sta-D-FDLA [corresponding to (3S,4R)-Sta-L-FDLA, 46.4]. The MS parameters used were as follows: DP −60.0, EP −7.0, CE −28.0, CXP −7.4, CUR 40, CAD High, IS −4500, TEM 750, GS1 40, GS2 40.

Workup

  1. customover 50 min
  2. customwere observed in both samples in a 1:1 ratio at tR 35.5 and 35.9 min

Sources & evidence

ORD record
ord-3d914649f2c04cfe85be81e34b022c1f
Source dataset
uspto-grants-2013_10
Patent number
US08569245B2

Reaction notes

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